Hello, everybody. It's Sam from the Financial Samurai Podcast. In this episode, I have a special guest with me, Emily Luck, co-founder and CEO of Plenty, a wealth platform for modern couples. Welcome to the show, Emily. Thanks for having me, Sam. In this episode, I would love to talk to you about your journey from college to your first job to working at one of the largest private startups and then leaving.

I've been in the Bay Area since 2001, and I've seen so many people join startups, make it big, but most don't make it big. Some join the big giants like Google and Facebook and Apple, and they end up very wealthy over a 10- to 20-year period. I'd love to understand your thought process and how you decided where to join after college and then your career trajectory after that.

Yeah, more than happy to chat through it. I think, you know, for me, it really did start with actually my family upbringing because both my parents and my grandparents, they'd each built companies for almost 20 years. And so for the longest time, that actually, to me, was the definition of starting a company.

When I was in university, I actually almost dropped out because I was just ready to start working. Instead, I ended up deciding to graduate early, but I had a chance to start working in venture capital, which for me, the VC world was so incredibly important because I was always an ideas person all the way through growing up.

But being in venture and the reason why I decided to start my career in venture, it gave me an opportunity to have a really analytical framework to understand what ideas can go the distance, what is something that I could potentially think about, you know, decades in my life of building and really think about that from the perspective of an investor.

I think one of the things that at the time someone had given me some really great advice and one quote that really stuck was, "Unlike an investor where you can make so many different investments, when you're working for a company, you're really making one bet at a time." And so if anything, it's even more important to think about whether or not that company is worth betting on.

As a venture capitalist, this is interesting because I think joining the VC industry after college is one of the most coveted types of industries to join along with investment banking, management consulting. How did you get the opportunity to join VC? And initially, you know, how did you gain the confidence to be a VC?

Because I've spoken to many VCs and there are builder VCs, VCs who've started companies so they know the operational, what it takes and also fundraising and all that. And then there are the MBA graduate case study VCs who have never built a company. And then, but then many of them still end up being successful investors.

Yeah. So for me, I've been doing small businesses, running little side hustles all of my life. Probably the more meaningful business was I started a company when I was in high school. It was selling customized clothing. It was a way to circumvent the fact that for public schools you had approved vendors, but student councils could circumvent that.

And so I've been building things like that pretty much all of my teenage years. And so I already had a track record, I think, of thinking about that framework of ultimately you could buy something or you produce something and what it costs you to use in order to produce that good or service is going to be less than whatever you're ultimately selling, hopefully a higher quality product or service for.

So that framework was something that was fairly deeply ingrained. I was really lucky that I had that chance to start off in venture. I was 20 years old at the time when I started. And during that time, actually, how I got that role was because I had worked on starting companies throughout university as well.

And I got involved with a student run venture fund. This was like back in the days before dorm room fund even existed. And we raised a small amount of money from a few other corporations with the intention. And we actually did invest into some student run startups. During that time, we also ran a number of different pitch competitions for students to actually pitch other VCs.

And I was one of the two people who was leading that at the time. And so when we invited actually some VCs to come to these pitch nights, I ended up meeting not only the person I end up going to work for, but actually also the person who is now currently one of our board members for plenty.

Oh, wow. That's fascinating. So it sounds like starting young and getting going and getting your hands and feet wet is one of the key strategies to getting into VC. I definitely would say that there's just no substitute for spending time amongst people who are in, you know, that world.

And one thing that I have seen is I have, you know, talked to many people who have come out of the business schools or the business programs and asked how to start. And there's actually a much lower barrier to entry than some people might think, because there's so many of these different events that are happening nowadays where you just go to the event.

There's, you know, tech meetups and all of that where there's other founders, other VCs. And it's a great environment to be able to learn from, but then also meet people. And I think one thing that's also been really helpful as a guiding principle for me my whole career has been that if you're looking to meet someone because you need someone's help or introduction right now, that's probably like a little late.

You really want to start getting to know people far before you ever even have an inkling of, oh, maybe I actually might need an introduction from them one day. So it really gives them time to build a more authentic relationship. Yeah, it's kind of like if you've been laid off from a firm and you start pinging people on LinkedIn, it's probably too late.

You need to be cultivating those relationships far in advance with no ask beforehand. Exactly. I think that's where you build the real relationships where people are willing to go to bat for you because they don't feel like you're there because you need something for them right away. Right. So how long were you doing VC before you moved on to, was it Stripe?

What was your road map after that? Yeah. So the original plan had been to stay in venture for a couple of years. I would say I've always had these three to five year plans and never actually followed through on the entirety of those plans. And life happens and I've kind of moved along with whatever comes through.

And so I stayed in venture for about a year and a half. But right around that time, I started noticing over the course of my first year in venture that a lot of companies that were, I was in venture in Canada, and most of the companies we invested in were Canadian companies expanding into the U.S.

market. And one thing I noticed was that most of our most interesting companies that also, to me, had the savviest technical teams, had the most interesting businesses or business models, they almost all use Stripe. And so one thing led to another. I had an individual that I'd known for a long time.

He coincidentally started working at Stripe and I just went to go visit. And I ended up joining them for a happy hour. He was like, "Yeah, come out to our office. I'll be working there. Let's catch up." And then one thing led to another. Turns out an individual that I'd sat next to was actually one of the business recruiters.

I didn't think too much of it. We had mostly just been talking about hobbies and interests. And then a couple weeks later, I got a message from them about the fact that they were starting to build out their business teams and asking if it was something that I'd consider moving out to San Francisco for.

What year was that? And at the time, do you recall what Stripe's valuation was? Yeah. So I moved out to join Stripe in 2015. And at that time, they had just closed that $5 billion round and they were about a 150, 200 person startup at that time. Wow. So $5 billion.

And so at the time, so you said you noticed the companies you were investing in were using Stripe more often. What was, I guess, the selling or the value proposition that made you say, "Okay, I'm going to change jobs and leave my city behind to come to San Francisco"?

I think one of the things that really jumped out for me for Stripe was at the time, there weren't really companies that were building great APIs for financial infrastructure. Stripe was really the first company to come along and do that. And when I actually started looking through the API documentation to really understand how revolutionary what they did truly was, if you had gone into a process where you're like, "I built a great product," or, "I have a company and we're trying to offer this service, and I'm just trying to get paid for my product or service." If you worked with most of the companies that accepted credit cards at that time, it was a convoluted process where the product didn't even work very well.

The documentation was terrible. They had all these limitations for what you could do. So they wouldn't even enable a lot of different business models, especially the marketplaces or platforms like Shopify or Lyft. And if you tried to get up and running with them quickly, their answer was, "Oh, let me put you through a sales process.

Fill out a sales form, have multiple sales calls." And if you think about from the mindset of a lot of people who are builders, they want to move quickly and they don't necessarily need to even have a sales call. They're just ready. They want to see the product. If it works, they want to go test it.

And Stripe really built for that. At the time, we used to talk a lot about arming the upstarts and really providing a product that helps support others, founders, and startups, and small business owners do whatever they need to do and not have all of the bureaucracy and all of the white tape.

And that was something that was, I think, such an important and vital part of Stripe because it made it possible where, yeah, within a week, you can start accepting payments for your product, which is so much of the lifeblood of what proves out a company. So for those who are unfamiliar with what Stripe does, what does it do and how does it make money?

Stripe started off being one of the first companies that made it really easy for any company in the world to accept credit card payments. Over the course of my time there, Stripe really evolved from being a pure credit card payments company to really providing a number of different financial infrastructure products, which also enabled you to move money between people or businesses, for you to open up bank accounts, for you to issue credit cards, for you to be able to set up subscription payments, fraud protection.

So a lot of the core infrastructure, if you're thinking about now moving money, either between people or as a business. And that was really something that has unfolded and is the analogy of a lot of times when people talk about AWS, for example, it's just core to a company being able to run.

So AWS is Amazon Web Services. And so I think for those who are familiar with FinTech and startups, Stripe is one of the largest private startups and it's not really a startup anymore. It's been around for a long time. At one point it rose to a almost a hundred billion dollar valuation during the boom in what 2020, 2021.

And now it's kind of come back to about 50 billion. So that's still 10 X when you joined. So I'm curious, how long did you end up being at Stripe and with so much success with Stripe, why did you decide to leave? Great question. So I was there for three years from 2015 through to 2018.

By the time I was making the decision about, you know, what to do next, the company was about 1,500, 1,600 people. It was a tough decision. I think, you know, I moved to San Francisco for Stripe at a time when also so much of my own social network were people at the company.

And so it was fairly immersive in terms of, you know, how I spent my time, who I spent my time with. And they're really good, kindhearted people, very smart, hardworking. And I really enjoyed getting to know and building lifelong friendships with a lot of people that I worked with.

So the decision to leave was actually even harder because of that. But ultimately for me, I known that, you know, the reason I had been excited to join Stripe at the beginning was because I thought it was a really great environment for me to learn a lot about a lot of different parts of running a company.

And the things that I would learn the most in at that chapter when they're about 1,500 to 1,600 people, and for that to grow to, you know, 3,000 or 5,000, the types of things I would learn would be less and less relevant to me actually starting a company one day.

And so that for me was a really big driver for that was just realizing even though it was a great company doing very well, great environment, what I would be learning would just be less, you know, relevant to what I was actually more excited to do down the road, which was ultimately build my own company.

Got it. That makes a lot of sense. Could you talk about the pay compensation, but you don't have to talk about your specific pay compensation, but how much were people getting paid in general for various ranks and how much of that was stock compensation? That's one question. And then the second question is when you leave a startup, what is the process like in terms of buying your options or RSUs?

Yeah, great question there. So it's not uncommon for people to over time, especially as the company raises more money, has higher valuations for the stock compensation to get to almost as much as, you know, 70, 80, 90% of your total compensation. That's not true though at the time when it's granted.

And so usually is somewhere in that, you know, 20 to 150% of whatever your salary is in terms of what you might be making from a stock compensation in that first year. What you're ultimately betting on is for that stock compensation value to grow because the company is doing well.

And so that's also where there is such, you know, a lopsided nature to how equity compensation works. The other thing that's also important is because even though, you know, a company might grow from call it 10 billion to a 20 billion valuation, usually the impact for an individual on their equity compensation is actually more than the 2X because there's also going to be a buffer built into it, which is at the time when you're granted, your shares, you know, are not considered to be liquid.

So that actually means that your shares are worth even less than what that last round is. So there's actually a lot of upside that usually is more than even just how much the valuation grows up by. Can you clarify that a little bit? So let's say I have $100,000 in stock options.

It's worth $10 billion, it goes to $20 billion. Are you saying I should think that my $100,000 is worth more than $200,000 or less than $200,000? Usually it would mean that it's more than $200,000 because when your stock options are granted and they're valued at $100,000, let's say at a $10 billion valuation, your stock price that the investors paid was $1.

But when you're holding that, actually when you pay for it, you won't be paying $1 because you can't actually sell. So that's what's called included, you know, the liquidity is taken into account for the value. So you as an individual, when you are granted that option, usually you'll be granted at a lower price, which might be, you know, if the investors paid $1, you might be paying $0.50.

Okay. And that's pretty common? That's fairly common, fairly industry standard for valuation practices, because as an employee, you actually don't have as much flexibility to be able to sell. So because you can't sell, that means, you know, you have a discount. That's also why when companies get closer and closer to an IPO, that discount usually decreases.

So, you know, any employee holding stock, it should get closer and closer to whatever the price an investor would pay. Hmm. Yeah. For folks listening, I'm sure many folks work at big tech companies or startups, and it seems very important for employees to understand what exactly they're getting and at what valuation.

Do you have any advice for employees who want to join startups on what they should ask their managers? Absolutely. So one of the most important things to ask is what the last 409A price is, or said differently, what is the strike price of the options you're granted? That is ultimately, you know, what price are you paying in order to buy your shares?

And that's something that a lot of times people don't ask. It's extremely important because that is ultimately, you know, as you think about how much money you have to pay to buy into the company, that's the amount, first off, that you need to pay. The other thing that's important is if you ever leave, you usually, the industry standard is that you get some number of months in order to then buy all of your shares.

And so if, let's say the price is really high, then it might make it even harder for you to leave one day, or it might be a reason why you might stay longer. That's not uncommon, you know, for people to end up being in this situation because they didn't ask.

The other thing, especially given the current landscape of startups, that I would highly recommend are for people to really deeply understand what were the prior fundraisers and valuations. Because right now we're in this really interesting time with startups where there are still a number of startups that raised at valuations one, two, or three years ago that were very high.

Based on what the current multiples are, and multiples in terms of what is the revenue times a multiple equals, you know, the valuation of a company, based on what the current multiples are, they're much lower in the market nowadays. And so if you're someone joining a company and it was valued at $200 million, well, if an investor were to put money in today, they might not think the company is, even after it's grown, worth $200 million.

And so that's where it really hits people who are joining the company, who might be in a situation where they are granted equity that isn't worth actually anything, potentially. Right. Yeah. It's just like if you're joining a company, you should put on your analyst hat and analyze the company's financials, expected growth, balance sheet, latest fundraising, and so forth.

Super important. That's definitely what I've thought about in the past when I was working. And now maybe same thing in the future. In terms of leaving Stripe, because I'm assuming that you were paid quite well, did you ever do like a model where you said, well, if I stay at Stripe for 10 years, I'm going to earn this base salary and get potentially XYZ stock compensation, and then maybe I'd be set for life.

How did you come up with that like financial decision to go leave Stripe and then join your own or start your own company? Great question. So for me, I definitely did think a lot about the fact that, you know, I would be leaving earlier, I would be leaving potential Stripe stock on the table.

And ultimately, the thing that I thought about there, and this has actually been a guiding, you know, North Star for me, my whole career was the value of what I can learn will have a much bigger impact on my future earning potential than necessarily the dollar that I earn right now.

That's been an important guiding factor, because actually, you know, when I even took the role in venture, for me, it was a role where I thought I would earn a lot more. I actually took a pay cut compared to what I could have earned at other job offers that I had.

But I just thought that in a venture environment, I would just learn far more. Even when I was joining Stripe from a cash salary compensation perspective, it was a cut based on other opportunities that I had at that time. It was actually, you know, almost 40 to 50 percent lower from a cash compensation perspective.

But I still thought it was worth it, because even, you know, an extra 20 or 40 or 50,000, when I thought about it, I was like, wow, it is a lot. But relative to the impact it could have on my future earning potential, it probably won't matter as much compared to if this opportunity I could learn, you know, twice as much or I had twice as much exposure to seeing how the best people in the industry do it.

So for me, that's always been a really important part of framing, especially, I would say, like career growth in your 20s and 30s. And so that was actually something that, for me, guided that. And ultimately, at Stripe, like, yes, it was a much more known amount in terms of what that option could be if I stayed.

But I thought I could just learn more and have the chance to do even more things hands on if I end up going to a smaller company. Right. So tell me or tell us about the path after Stripe. Yeah. So I ended up getting pretty lucky where one of the early investors in Stripe had ended up introducing me to one of the companies that I ended up going to afterwards.

I pretty much had had a conversation where I was like, you know, I'm really looking for a much earlier stage team. And I really want to go to a company where I feel deeply connected to the mission of what the company is doing. Stripe was at a point where they were starting to build for larger enterprises, which is extremely valuable and important.

But for me, I've just always been driven by more of the stories of individual humans and people and families. And so I knew I wanted to build a product that was ultimately a consumer product at the end of the day. I ended up joining this company named Even right around when they were 30 people initially joining as chief of staff.

And then I stepped into an acting CEO role there. The company was really focused on helping individuals living paycheck to paycheck reach a point of financial stability. And I like to joke that I had the best values interview that any startup probably could have had because I ended up actually meeting my life partner and now my co-founder there.

And we had both joined for the mission. Got it. And how long were you at Even? And how did that, I guess, journey and compensation compare to if you had stayed at Stripe? Yeah. So for that, because of the role that I was in, I was in a more senior role.

We ended up selling the company to Walmart and won. And so from an acquisition and exit perspective, it was, you know, a pretty solid startup exit. We ended up selling the company into this big entity that is Walmart's new entrance into banking. And as I think about, you know, part of this is from an opportunity perspective, part of this from a compensation perspective, I think it ended up working out.

The ultimate part, though, was that the type of experience that I had, because I was effectively the CEO's right hand, I ended up being able to further build, you know, the people that I got to know, really get to see firsthand how to operate at an executive level. You know, we were there as a company was about 30 people to over 120 people.

And so the exposure and experience I got was one where I probably wouldn't have gotten an equivalent amount of exposure to kind of being firsthand making the decisions, being firsthand in all of the most important meetings as I would have had I stayed at Stripe. And so that experience was ultimately the most important thing for me ultimately getting the confidence to be like, oh, I think I'm ready.

I don't think I actually have another startup that I want to go get more experience at. I think I've, you know, seen how some companies are built and there's no time like now and now is the right time to build a company like Plenty. Yeah. I mean, that's a great arc because I think joining Stripe in 2015 and then watching it 10x or more was kind of a really good move, right?

Pretty lucky, pretty auspicious. And then joining even at 30 and then selling to Walmart, probably for a multiple of the valuation where you join at was also a good move. And so could third time be the charm? Well, it's been two times already. So let's talk about Plenty. When did you all start and how difficult or easy was it to come up with the idea to help modern couples manage their money?

And also how difficult or easy was it to raise capital and get other people to believe in the mission? Yeah. So Plenty was started two years ago and it really started out of a lot of frustration that Channing and I had had when we started trying to merge our finances after we got engaged.

We were trying to answer what felt like fairly straightforward questions like, where should we put our money? How much do we need for a house? What happens if we have two kids or three kids or four kids and what does that look like in terms of what we would need to support that?

And the thing that was crazy was we were like, we're not the first ones to ask these questions. So many couples have asked these questions, are asking these questions. So surely there must be great products and solutions for this. The thing that was mind blowing for us was we tried every product and we're like, wait a second.

Almost all of the products that we can see from the last generation of FinTech only really work for you to use on your own. They have all these, you know, I'm not going to name names here, but there's definitely companies that have joint products where both people can't even deposit.

You have companies that offer, quote, family plans, but they don't even offer joint accounts and there's no shared visibility. So we started seeing all these broken holes where we were like, wait, we know that modern couples want to work together a lot more than the tools enable that right now.

So that was a really big starting point for us. Another starting point too was we started, you know, meeting, we actually found this list of Forbes top 40 financial planners for millennials. And we were like, well, let's just see what that's like. Maybe that is a good solution for our generation.

And after interviewing with about 20 of them as a prospective client, we just got fired up because we had people, what it felt like selling a snake oil where we were like, wait, we both come from a background in finance. You know, I have my CPA and my CFA Channing has a degree in finance and economics.

And we were like, you're just throwing buzzwords at us to make it feel like we should trust you and pay you either thousands of dollars, a couple percent. You know, we had one person even try to pitch us on three percent of our annual income in order to work with them as a client.

And this was one of the people on the top list too. And we were just shocked that we were like, this can't be the solution for people who are just trying to do the right thing with their money. It needs to be a lot more affordable. And it also is just a different service offering.

People I think don't want to talk to humans to the same degree and say that every single question you have, you don't have the ability to answer it on your own. You have to talk to a human and email them. And then, by the way, also pay them, you know, five thousand dollars a year.

Right. So that was a really big core for what started, you know, things. And then ultimately, one of the things that we also believe in deeply is over the course of the next 10 years, we believe that because of the last generation of fintech and especially fintech infrastructure, there will be a small number of companies that really challenge the Wells Fargo's, the Schwab's, the big banks in the U.S.

and are actually able to challenge them because they've built a much better product offering that all works together. Your taxes are integrated with your investing, which is integrated with how you apply for your mortgage, which integrates with how you manage your day to day spending and saving. And we believe that will be built and aim to make plenty one of those companies.

Awesome. So for 2024, let's say second half of 2024, what can plenty provide couples today? And where do you see the roadmap over the next three to five years? Great question. So right now, couples can come in and have one place where they can see what they have together as well as what they have on their own.

We treat every partnership as a partnership plus two individuals. And so you have this visibility into not only all the accounts that you have not at plenty, but also your spending, your saving and investing and your income. From there, we know that one of the big drivers for couples and one of actually the most positive moments of talking about money is really talking about the goals that you share and want to work on together.

So we offer plenty investment accounts so you can easily save or invest towards a home renovation, a home down payment, maybe for your kids to go to college for your retirement. And so we will actually help you stand up both investing and saving where our savings product today, you know, interest rates always change, but right now it's the 5.1 percent rate.

And we also have a more advanced stock portfolio that we put together for you that uses individual stocks instead of ETFs in hopes that it ends up actually reducing future taxes that you might pay. And very much our mental model for all the investment products that we offer are really looking at what you would get if you worked with a wealth manager.

But for most everyday families, they don't even know to ask for much less. They don't even know that it could be right for them or how to access it. So that's a bit of a framework for how we've thought about what products we will have as part of our upcoming launch.

And then for the rest of this year, we're really excited to bring banking to the forefront as well, so you can also offer a plenty checking account as well as a savings account. And you will also be able to manage your taxes, too, from Plenty. Got it. Sounds like a lot is ahead and sounds really good.

In conclusion, can we talk a little bit diving down deep into joining a startup? Because I know a lot of listeners here might also want to move to San Francisco or some big city and join a startup and leave their boring career behind where they're not learning much of anything and they're just doing the same old thing over and over again.

What are your thoughts about joining a startup at various stages of funding? For example, pre-seed, I guess seed series A, B, C, D, and then I guess eventually IPO, which is not a startup. Yeah, so I would say this with, you know, very much a lot of awareness that I've been incredibly lucky with the companies that I have ended up joining.

I think also one thing is at every step when I made the decision to join a startup, for me it wasn't just joining any startup or taking any job. I talked to a number of different companies and opportunities. I really evaluated every startup as if I were an investor who could only make one investment.

And so I don't think all startup jobs are necessarily equal. I think it's helpful to have a foot in the door for your initial startup, if especially if you're moving from another city where there might not be as much of a startup or tech presence. But ultimately I would say very early on, it matters a lot if you're at a company that has seen growth.

And so being very analytical, even if it's necessarily, you know, the perfect role, I would take not having the perfect role at a startup that is growing quickly any day over "the perfect role" at a company that isn't growing. Because what ends up happening is you end up spending a lot of your time and a lot of the experience you gain is not actually solving growth problems.

And it also is a bit more of like a strange dynamic where at Stripe, it was so collaborative because the company was growing so quickly, where everyone was just trying to help each other because ultimately we were trying to help the company and everything, like we needed all hands on deck.

And what I've also seen is sometimes when people join companies that don't grow as much or aren't growing at all, it ends up actually creating a lot more of pressure where instead of everyone pointing forwards, you end up having a lot more internal politics and a lot more internal dynamics because ultimately it's not solving the problem that, you know, the company isn't growing or there's other issues that are bigger with the company.

So especially if you're earlier on in your career, I'd recommend like say yes to a seat on something that is growing quickly. I think my original title was like a sales analyst accountant. It was like a hodgepodge title, but it was like, I'll take whatever seat and I'll just once I get there, like I'll do whatever we need, which I think is absolutely the mentality that is, you know, helpful and you also learn the most in while you're joining something.

Got it. Well, it's been a great journey, Emily, and I wish you best of luck with plenty. Thanks again for joining the podcast and sharing your wisdom about the startup world. Thank you so much for having me, Sam. All right. Take care and we'll speak again. All right, everyone.

If you enjoyed this podcast, I'd love a share, subscribe and a positive review. It helps keep me going. Every single episode takes hours and hours to produce. If you want to keep in touch, check out the Financial Samurai newsletter at FinancialSamurai.com/news. Talk to you all later.